JP6702917B2 - 高流動水素化スチレン−ブタジエン−スチレンブロックコポリマーおよび用途 - Google Patents
高流動水素化スチレン−ブタジエン−スチレンブロックコポリマーおよび用途 Download PDFInfo
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- JP6702917B2 JP6702917B2 JP2017156467A JP2017156467A JP6702917B2 JP 6702917 B2 JP6702917 B2 JP 6702917B2 JP 2017156467 A JP2017156467 A JP 2017156467A JP 2017156467 A JP2017156467 A JP 2017156467A JP 6702917 B2 JP6702917 B2 JP 6702917B2
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- Prior art keywords
- styrene
- block copolymer
- butadiene
- poly
- melt flow
- Prior art date
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- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 title description 5
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical class C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 title description 4
- 239000012530 fluid Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 70
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 59
- 229920001400 block copolymer Polymers 0.000 claims description 53
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 46
- 229920006132 styrene block copolymer Polymers 0.000 claims description 35
- -1 poly(styrene-butadiene-styrene) Polymers 0.000 claims description 33
- 239000000835 fiber Substances 0.000 claims description 30
- 239000000155 melt Substances 0.000 claims description 27
- 238000009826 distribution Methods 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
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- 239000004745 nonwoven fabric Substances 0.000 claims description 9
- 239000002174 Styrene-butadiene Substances 0.000 claims description 8
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 239000011115 styrene butadiene Substances 0.000 claims description 8
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 8
- 238000001175 rotational moulding Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- DAONBNNRBFCSLS-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 DAONBNNRBFCSLS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 3
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- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 claims 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 4
- 229920006271 aliphatic hydrocarbon resin Polymers 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920013640 amorphous poly alpha olefin Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 4
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000013032 Hydrocarbon resin Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
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Description
ブロック状%=100×(ブロック状スチレン単位/全スチレン単位)
ポリマー−Bd−S−(S)n−S−Bd−ポリマー(式中、nはゼロより大きい。)のように表されるものは、ブロック状スチレンと定義される。例えば、上の例においてnが8に等しい場合、ブロック状化指数は80%になるであろう。ブロック状化指数は、約40未満であることが好ましい。10重量パーセントから40重量パーセントのスチレン含有量を有するポリマーの一部については、ブロック状化指数が約10未満であることが好ましい。
高メルトフローhSBSポリマー
hSBS:シクロヘキサン201kgおよびスチレン9.1kgを約50℃の80ガロンのステンレス製反応器に投入した。次に約12重量%のs−ブチルリチウム2428mLを反応器に投入して重合を開始した。スチレン重合が完了するまで約50℃で進行させ、GPC用にサンプルを採取した。このステップにおける分子量は、4.8kg/molであることが明らかになった。さらにスチレン0.38kgを加えて重合させた。このポリマーをGPCで分析したところ、分子量は5.0kg/molであることが判明した。ブタジエンは、約1kg/分の速度で加えた。ブタジエンの段取りを開始して1分未満で、1,2−ジエトキシプロパン198グラムを加え、次いでブタジエンの添加速度を1.5kg/分に上げた。合計36.05kgのブタジエンを加え、温度を約50℃から55℃の間に保ち、重合が完了するまで継続した。このステップの終了時に採取したサンプルは、分子量26.0kg/mol、1H NMRによるビニル含有量は73.7%、ポリスチレン含有量は24.1%であった。次に、メチルトリメトキシシラン114mLを加えることにより、S−Bジブロックポリマーをカップリングさせて、ジブロック鎖の94%がカップリングしたポリマーを生じさせたが、この大部分(82%)は直鎖状であり、残りの部分は主として3本の腕がある放射状の化学種である。メタノール55mlを加えて、停止するようにした。次いでこのポリマーについて、残った0.12meqオレフィン/gの不飽和を、Co/Al触媒(Al:Coは1.7:1(mol/mol)、Coは約22ppm。)を用いて、700psiの水素下、85℃で水素化し、選択的に水素化されたスチレン−ブタジエン−スチレンポリマーを生成した。全ポリマー溶液125kgのうちの約60kgは最初のバッチ投入で加え、残りの部分は、所望の範囲内に反応温度を保つのに必要な速度で加えた。N2/O2混合ガスでスパージしながら、セメントを水性のリン酸に接触させることにより、触媒を酸化および抽出した。さらに、カプリル酸約100mlを加えた。次に、アンモニアでスパージすることによりセメントを中和して脱イオン水を用いて洗浄し、さらにEthanox330(ポリマーベースで0.2重量%)およびIrgafos168(ポリマーベースで0.3重量%)を加えることにより安定化させた。生じた本発明のhSBSポリマーは、220g/10分のメルトフローレートを有していた。
[実施例2]
繊維ガラスマットおよびスクリム
本発明の技術は、製造および健康、安全ならびに環境の面で著しく改善されると共に、繊維ガラスマットおよびスクリムを含む複合材に耐衝撃性および向上した靭性をもたらすと期待される。100g/10分以上のメルトフローレートを有する本発明のhSBSまたはhSBSSは、十分に高い分子量を有するため揮発性がなく、優れた弾性および靭性を示す一方で、高流動特性により、メルトブロー繊維、布または低坪量フィルムとしての応用が可能になる。靭性、弾性があり、高流動のhSBSまたはhSBSSと繊維ガラスマットまたはスクリムとを組み合わせるための異なる工程を少なくとも3つ想定することができる。
1.13.5osy−オンス/平方ヤード(約450g/m2−グラム/平方メートル)チョップド繊維ガラスマットをUS Composites社より購入した。このタイプのマットは一般に、金型、自動車およびボートの建造用途に用いられる。このマットは、十分な靭性を持たせるために通常24osyの樹脂を必要とする。
hSBSフィルムを、Killion製フィルム押出機にて温度設定を300−330−360−370°Fに、ダイの設定を370°Fにして押出した。
低粘度被覆
低粘度ポリマー(上述のhSBSおよびhSBSS)は、VOC(揮発性有機炭素)の規制を満たさなければならない用途において重要である。hSBSは高メルトフローレート(低粘度)を有し、これを他の低粘度ポリマーと比較した。4種類のVOC除外溶媒のみ、即ち酢酸メチル、p−クロロベンゾトリフルオリド、酢酸t−ブチルおよびアセトンをhSBSと共に検討できることが明らかになった。非VOC規制が許容される分野においては、低粘度ポリマーに適合する任意の非除外溶媒(除外されていない有機溶媒)を用いてもよい。例示的な非除外溶媒には、Aromatic 100(軽質芳香族ナフサ)、Aromatic 200(重質芳香族ナフサ)、キシレン、トルエンなどがある。溶媒(除外、非除外、またはこれらの混合物)のブレンドおよび本発明のhSBSまたはhSBSSのスチレン系ブロックコポリマーを少なくとも40重量%含む被覆は、450グラム/リットル未満、好ましくは350グラム/リットル未満、より好ましくは250グラム/リットル未満のVOC含有量を有する。
キシレンおよびVOC除外溶媒のp−クロロベンゾトリフルオリド(PCBTF)を含む溶媒ブレンドの溶液粘度を測定した。溶液は、G1643およびhSBSポリマーを用いて、固形分15、20および25重量%で作った。結果はセンチポアズ(cps)で測定した(表3参照)。G1643と比べてhSBSが最も低い粘度を有していた。粘度は、溶液中においてPCBTFがキシレンを置き換えるにつれて上昇する。
白色のエラストマー屋根被覆には、VOCが250g/リットルを超えてはならないなど、さらに厳しい要件がある。白色のエラストマー屋根被覆を配合してG1643およびhSBSポリマーの溶液粘度を比較した。配合は、VOC250グラム/リットルを満たすことを目標とし、全ての原料の濃度を重量%で一覧にした。粘度の低減は、塗工坪量および被覆の乾燥時間に対して著しい効果がある。hSBSは、G1643よりも特性が適しており、粘度が低い被覆の配合が得られた(表4参照)。エラストマーの屋根被覆に関する要件は、ASTM D6083に記載されている。粘度の要件は、ASTM D562のメソッドA、手順Aに従った測定で、85から141cpsである。
接着性配合物
既に述べた通り、APOベースの接着性配合物は低コストおよび低性能である。しかし、これらは吹付が可能で、幅広い物品に適用できる。APO接着性配合物の性能は、本発明のhSBSとブレンドすることにより、少なくとも中位の性能にまで改良することができる。100g/10分未満のメルトフローレートを備えるSEBSポリマーに基づく、従来のSEBSベースの配合を含む中位の性能を持つ多くのポリマーとは異なり、この配合物は依然として吹付が可能である。接着性配合物は、感圧接着材、ホットメルト接着剤、建築用接着剤、弾性接着剤などにおいて有用である。概してこれらの配合には、本発明のスチレン系ブロックコポリマー、ポリ−アルファ−オレフィン樹脂、粘着付与樹脂、および鉱油、酸化防止剤などの任意選択の原料が含まれる。通常、これらの組成物には、上記組成物の約30から約80重量%だけ存在するポリ−アルファ−オレフィン、上記組成物の約10から約35重量%だけ存在するスチレン系ブロックコポリマーhSBSおよび/またはhSBSS、ならびに上記組成物の約20から約60重量%だけ存在する上記粘着付与樹脂が含まれる。
標準的な剥離、粘着、凝集および粘度試験を、これらの配合物に対し、感圧テープ評議会(Pressure Sensitive Tape Council)(PSTC)による感圧テープに関する試験法マニュアル(Test method manual for Pressure Sensitive Tapes)、感圧材料に関する標準FINAT試験法(standard FINAT test method for Pressure sensitive materials)、感圧接着テープに関するAFERA試験法(AFERA test methods for Pressure Sensitive Adhesive Tapes)および関連するASTM法に記載の通り実施した。適用における配合物の機能を明らかにするために、異なる試験表面を用いた。即ち、FINATにより推奨されているクロムめっきしたステンレス鋼板(No.304「ss」)およびクラフト紙である。
本発明における接着剤組成物の調製工程には特定の制限は課されない。従って、ロール、バンバリーミキサーまたはDalton社ニーダーを利用する機械的な混合工程、撹拌機、高剪断Z翼ミキサー、一軸または二軸スクリュー押出機を備えた溶融ケトルを用いることにより加熱および混合が行われることを特徴とするホットメルト工程、コンパウンド成分が適した溶媒に注入され、撹拌されることによって、感圧接着組成物の均質な溶液を得ることができる溶媒工程など、任意の工程を用いてもよい。
身体衛生用途向けフィルムおよび不織布の実施例。
スラッシュおよび回転成形の実施例
本発明のポリマーhSBSをベースとする化合物は、スラッシュ成形工程および回転成形工程のように剪断が小さい工程で用いられるとき、改善された溶融特性を示す。スラッシュ成形および回転成形化合物の典型的な配合は、表10で参照することができる。
Claims (7)
- メルトブロー弾性不織布であって、当該不織布は、230℃および2.16kgの質量で100g/10分を超えるメルトフローレートを有する選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマー繊維を含み、50g/m2の前記メルトブロー弾性不織布が、70%を超えるヒステリシス回復エネルギーおよび20%未満の永久歪みと共に、200%を超える伸びを示し、当該ブロックコポリマーは、18%から45%の間のPSC、73.7%から80%のビニル含有量、および60%から97%のカップリング効率を有し、
当該不織布は、熱可塑性ポリマーを含んでなる少なくとも1つの追加の不織布層をさらに含み、
当該不織布は、吸着性の身体衛生製品の構造物内に用いられる不織布積層構造物を形成し、
当該吸着性の身体衛生製品は、赤ちゃん用おむつ用品、成人失禁用品および女性用ナプキン用品から選択され、
当該不織布層は、スパンボンド、2成分スパンボンド、メルトブローまたはボンデッドカーデッドウェブ層から選択される、
メルトブロー弾性不織布。 - スラッシュ成形、回転成形、射出成形またはカレンダー仕上げされた物品であって、230℃および2.16kgの質量で100g/10分を超えるメルトフローレートを有する選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマーを含み、当該ブロックコポリマーは、18%から45%の間のPSC、73.7%から80%のビニル含有量、および60%から97%のカップリング効率を有し、
当該物品は、210℃および2.16kgの質量で40g/10分を超えるメルトフローレートを有する高流動ポリオレフィン、ポリイソブチレン、ポリブテン、および熱可塑性コポリエステルから選択されるさらなる成分を含む、物品。 - 230℃および2.16kgの質量で100g/10分を超えるメルトフローレートを有する選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマーの水性エマルジョンであって、当該ブロックコポリマーは、18%から45%の間のPSC、73.7%から80%のビニル含有量、および60%から97%のカップリング効率を有し、当該ブロックコポリマーは、マレイン酸無水物で官能化されている、
水性エマルジョン。 - 繊維または繊維の束に結合された選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマーで被覆されたこれらの繊維または繊維の束であって、前記ブロックコポリマーが、230℃および2.16kgの質量で100g/10分を超えるメルトフローレートを有し、および前記繊維または繊維の束は、ガラス、炭素またはアラミド繊維であり、およびさらに前記ブロックコポリマーはマレイン酸変性されており、当該ブロックコポリマーは、18%から45%の間のPSC、73.7%から80%のビニル含有量、および60%から97%のカップリング効率を有する、繊維または繊維の束。
- スラッシュ成形または回転成形された物品であって、当該物品は、選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマー、ポリ−1−ブテン、ポリプロピレンおよび鉱油を含む組成物を含み、当該ブロックコポリマーは、230℃および2.16kgの質量で100g/10分を超えるメルトフローレートを有し、かつ、当該ブロックコポリマーは、18%から45%の間のPSC、73.7%から80%のビニル含有量、および60%から97%のカップリング効率を有する、物品。
- スラッシュ成形または回転成形用組成物であって、当該組成物は、選択的に水素化されたポリ(スチレン−ブタジエン−スチレン)ブロックコポリマーまたは選択的に水素化された制御分布ポリ(スチレン−ブタジエン/スチレン−スチレン)ブロックコポリマー、ポリ−1−ブテン、ポリプロピレンおよび鉱油を含み、当該ブロックコポリマーは、230℃および2.16kgの質量で100g/10分から220g/10分のメルトフローレートを有し、かつ、当該ブロックコポリマーは、45,000の直鎖の真の最小分子量;18から45%の間のPSC;73.7から80%のビニル含有量;および60から97%のカップリング効率を有する、組成物。
- 請求項6に記載の成形用組成物であって、当該組成物の100重量%に基づいて、当該ブロックコポリマーは50から70重量%の範囲で存在し、当該ポリ−1−ブテンは10から15重量%の範囲で存在し、当該ポリプロピレンは8から11重量%の範囲で存在し、および当該鉱油は7から10重量%の範囲で存在する、組成物。
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US20130225020A1 (en) | 2013-08-29 |
BR112014020022A2 (ja) | 2017-06-20 |
KR101680441B1 (ko) | 2016-11-28 |
JP2016128622A (ja) | 2016-07-14 |
EP3381953A1 (en) | 2018-10-03 |
EP2817371B1 (en) | 2018-07-18 |
JP2015513584A (ja) | 2015-05-14 |
EP2817371A1 (en) | 2014-12-31 |
US20140364532A1 (en) | 2014-12-11 |
WO2013148024A1 (en) | 2013-10-03 |
TWI561602B (en) | 2016-12-11 |
JP2018035490A (ja) | 2018-03-08 |
BR112014020022A8 (pt) | 2017-07-11 |
US20160102164A1 (en) | 2016-04-14 |
US9359523B2 (en) | 2016-06-07 |
JP6001685B2 (ja) | 2016-10-05 |
US9249335B2 (en) | 2016-02-02 |
TWI595061B (zh) | 2017-08-11 |
CN104379667A (zh) | 2015-02-25 |
US9637660B2 (en) | 2017-05-02 |
US20140364555A1 (en) | 2014-12-11 |
CN107057260A (zh) | 2017-08-18 |
TW201602279A (zh) | 2016-01-16 |
CN107057260B (zh) | 2020-03-06 |
KR20150012237A (ko) | 2015-02-03 |
TW201339268A (zh) | 2013-10-01 |
JP6321055B2 (ja) | 2018-05-09 |
US20140371377A1 (en) | 2014-12-18 |
EP2817371A4 (en) | 2016-04-13 |
US9243163B2 (en) | 2016-01-26 |
CN104379667B (zh) | 2017-02-22 |
EP3381953B1 (en) | 2020-04-01 |
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